No matter who you are – first dates are ALWAYS a challenge. To ensure the best possible experience for everyone, here are twenty things for you to keep in mind or avoid on that first date. Most of this is pure common sense, but you’d be surprised how often we men forget about some of this stuff – or just do things without fully thinking through the possible implications …


  1. Don’t be late
    The fastest way to make a poor impression on a first date is to be late. If something beyond your control causes you to be late, then give your date a phone call to let her know what is up.
  2. Don’t forget to brush your teeth and be clean overall
    Nasty teeth are one of the biggest turnoffs imaginable so definitely make sure yours are clean … and that the rest of you, and your car, etc. are clean, too. Be cognizant of your breath especially!
  3. Don’t show up with flowers
    I’ll probably take some heat from women on this one – but I think that showing up with flowers on a first date is just wrong and possibly pathetic. It can make you seem over-anxious … or it might set the woman’s expectations artificially high in the future. Best to wait on the flowers until a relationship is definitely moving forward. [If you need help on the subject of flowers, be sure to see the dedicated article here called When to Send a Woman Flowers]
  4. Don’t over-dress nor under-dress
    Some people say you can never be over-dressed – but you definitely can. Dress appropriately for your age, and for where you are taking your first date.
  5. Have a plan for the date, but be flexible about it
    Don’t overthink your first date. Have a plan but be flexible about it. The more carefully you plan something, the more likely you are to become concerned if things deviate from the plan … so just go easy, and focus on getting to know her … and having a nice evening together no matter what the situation.
  6. Don’t drink too much during the date
    Drinking too much on your first date with a woman is likely to make her think that you are either an alcoholic or that you are just a major party person. A better plan is to stop after several drinks. Of course, if she is drinking like a fish – you can always go with the flow, and see where it takes you ;o)
  7. Don’t talk about yourself
    Talking non-stop about oneself is the biggest first date-killer in the world. A better bet is to get your date talking about what she likes, and then you can figure out what you might have in common.
  8. Avoid discussing previous relationships
    Never discuss prior relationships during a first date. If she asks, then keep your response very brief and polite about your ex.
  9. Don’t discuss DEBATE religion or politics
    Religion and politics are two of the most sensitive topics you can discuss with anyone – so your absolute best bet on any first date is to avoid DEBATING these topics. And if you cannot avoid them, then tip-toe … which means don’t speak of them in a judgmental fashion. Per Nickolaus’s comment at the end of this article – I now think it is better advice to not debate religion or politics (versus not bringing it up to begin with). By at least discussing these controversial topics, you might uncover some potential incompatibilities. I inserted in ALL CAPS the word “DEBATE” and “DEBATING” into the original #9 and in the first sentence … just so you can see how my advice is evolving as a function of excellent feedback. These are also things that can be discussed in our Midlife Forum … ;o)
  10. Don’t forget to LISTEN to what she is telling you
    You won’t have to listen to her AFTER you’ve had sex with her, so at least listen once – during your first date. [Clearly, I am joking here. ha ha ha]
  11. Don’t take phone calls or respond to text messages during your date
    Your date deserves your undivided attention – whether it is your first date or not. Don’t disrespect her by taking cell phone calls or reading or returning text messages during your date … it is just rude!
  12. Don’t eyeball or flirt with other women
    Women are extremely sensitive to eyeballing or flirting with other women – so be careful not to do this!
  13. Be a gentleman but don’t go overboard
    Being a gentleman means opening the door for her … letting her order her meal first … and the like. Just don’t go overboard with it.
  14. Don’t forget to compliment her, and don’t go overboard
    You definitely want to say at least one nice thing to her during your date – but don’t be overly complimentary because it will make you look over-eager. The safest thing to tell her (once) is how nice she looks – right when you pick her up or first meet her.
  15. Don’t order something drastic for dinner compared to your date
    Skip the pork ribs, or the crab legs – don’t order something that requires too much work or mess … as it won’t turn on your date.
  16. Don’t be too judgmental
    Sometimes people are just a bit nervous on that first date – so be careful not to form your opinions about her too quickly. That said – do trust your instincts … I’ve absolutely learned that in the past!
  17. Don’t ask her to pay for the date, or for her “half”
    Being cheap is the quickest way to relieve yourself of the responsibility for a subsequent date.
  18. Don’t be rude to anyone during the date
    Be nice to everyone – including the restaurant staff, the valet, EVERYONE … otherwise you run the risk of being viewed as rude (whether situationally-justified or not).
  19. Don’t assume too much about your possible relationship with her
    A first date is just that – so don’t decide that she is going to be your next wife. Just take things slowly – and one step at a time. Of course, if she invites you in for a drink and takes off her top – then do what you must, but don’t be too presumptive about a possible relationship.
  20. Don’t try to get into her pants on the first date unless you are sure that is what you both want
    One motto explained in many places in the Dating Advice section of this site states that you should ALWAYS GO FOR IT … which means you should feel free to push the envelope of the situation you are in. This doesn’t mean that you should insist on sex at the end of that first date … but it does mean that if she is giving you all the right signals that you should not be afraid to kiss her, and see where that leads.
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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.